Aldrin

Jonah
3-aldrin.jpg

Basic Information

IUPAC Name
1,2,3,4,10,10-Hexachloro-
1,4,4a,5,8,8a-hexahydro-
1,4:5,8-dimethanonaphthalene
Molecular Formula
C12H8Cl6
Molar Mass
364.91 g/mol
Melting Point
104 degrees Celsius
Boiling Point
145 degrees Celsius
Natural State
Colorless Solid
Density at Natural State
1.7 g/L at 20 degrees Celsius
Solubility: 0.027 mg/L
Soluble in water, petroleum, acetone, benzene, xylene, and extremely soluble in fats. It will dissolve much better in carbon-containing compounds than in water.

Structure

Percent Composition:
  • By number: 23.08% Cl, 30.77% H, 46.15% C
  • By mass: 58.3% Cl, 2.21% H, 39.5% C
Contains mostly single, but some double bonds.
It reacts with oxygen to create epoxide dieldrin.



The Story:


In 1928, a German chemist by the name of Kurt Alder and his partner, Otto Paul Hermann Diels, made a scientific breakthrough that led to the discovery of the Diels-Alder reaction. This was an entirely new type of reaction, which involves the combination of a conjugated diene and a substituted alkene. The result is a cyclohexene. Today, it is considered to be one of the most useful reactions in organic chemistry. This is because it does not take much energy to form a cyclohexene ring, and cyclohexene rings are useful in many other different types of reactions. Diels and Alder won the Nobel Prize that very year for this revolutionary discovery.

Between 1946 and 1976, over 270 million kilograms of aldrin were produced using this reaction. It is a powerful organochlorine insecticide. It was used mainly to treat seed and soil for the prevention of damage from insects. While on the ground or inside insects, aldrin oxidizes into a different substance, epoxide dieldrin. Epoxide dieldrin is even more harmful to insects. Aldrin became an increasingly popular pesticide until the 1970's, when it was banned in most countries. The reason for this was that aldrin and all other cyclodiene were known as strong pollutants to soil, water and crops. It is also extremely toxic to animals, such as rats and fish. It was so dangerous because its solubility in water is extremely low, at 0.027 mg/L. It was eradicated in the United States in 1974, however, it is still used in developing countries.

Aldrin is very harmful to humans and the environment. It can cause severe respiratory irritation, headaches, dizziness, nausea, vomiting and diarrhea.

How is it Made?


Aldrin is not extracted from the environment as a natural resource in any way shape or form. It is a purely synthetic compound, and is synthesized by the combination of hexachlorocyclopentadiene and norbornadiene via a Diels-Alder reaction. It has one isomer, called isodrin. Isodrin is made from the synthesis of hexachloronobornadiene and cyclopentadiene. It is also a strong insecticide. Both of these compounds used to be made in labs for use as pesticides, but not anymore, since they are banned.

Uses:


  • pesticide/insecticide
  • control soil insects
  • protection of wooden structures (from insects)



3D Molecular Structure (iMol)Aldrin-from-xtal-3D-sticks.png


3D Molecular Structure Viewing Instructions

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